Transition-Metal-Free С–С Coupling of 5,7-Dihydroxybenzopyrones with Quinoxalones and Pteridinones

Abstract

A new synthetic protocol for nucleophilic substitution of hydrogen­ in quinoxalones and pteridinones by the action of 5,7-di­hydroxycoumarins and related m-dihydroxybenzene compounds has been developed. The C–C coupling reaction proved to proceed smoothly under rather mild conditions, thus giving the corresponding C–H functionalized products in good yields. The advantages of this environmentally benign protocol are high regio- and chemoselectivity, and an easy workup procedure. Direct incorporation of the coumarin moiety into the pyrazine ring in pteridines or quinoxalines provides a short pathway to pyrazine-coumarin hybrid compounds.

Key words

metal-free coupling - halogen-free coupling - pteridines - quinoxalines - C–H arylation - substitution of hydrogen

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